Vacation rentals in Winchester

Guest suite in Winchester

A kitchenette area features wooden cabinetry and a full-size refrigerator, complemented by a microwave and coffee machine. A love seat with floral cushions sits next to a window, allowing natural light to illuminate the oak hardwood flooring. A small dining table is placed nearby.

5 out of 5 average rating, 215 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

5 out of 5 average rating, 16 reviews

A glass-paned door allows a view into a hallway leading to a well-lit kitchen. The hardwood floor extends into the space, and light fixtures along the ceiling provide illumination. Soft ambient light is seen towards the back, suggesting a welcoming atmosphere.

Apartment in Winchester

Winchester Apartment on Greenway

Updated apartment with hardwood floors, full kitchen and washer/dryer, next to Davidson Park, Tri-Community Greenway and the Community sport complex. A wonderful short walk down the Greenway takes you to Leonard Pond for tennis, pickleball, soccer or frisbee. A 20-minute walk down the Greenway takes you to Winchester Center for restaurants, shops and train to Boston. Or walk four blocks east to explore the 2,000-acre Middlesex Fells Reservation. Route 93 access is less than a 5-minute drive.

4.98 out of 5 average rating, 201 reviews

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

4.63 out of 5 average rating, 35 reviews

An inviting bedroom is showcased, featuring two queen-size beds with white linens. A brick fireplace serves as a focal point, and a wooden desk and chair are positioned beside a window, allowing natural light to illuminate the space. The walls are painted in a soft yellow hue.

Home in Winchester

House on A+ school area w/AC & W/D

Fabulous opportunity to stay in a prestigious school area & a historic residential town of Winchester, MA. It’s in a beautiful, quiet, & safe neighborhood on the west side of Winchester, MA, near Lexington, Arlington, & Woburn towns. Close to historic landmarks, restaurants, elementary school, highway, & public transportation. The in-law suite with a separate entrance is part of a single-family house on the back of an A+ elementary school. Relax with your friends & family at this peaceful place

4.95 out of 5 average rating, 191 reviews

A spacious living area is presented with a comfortable sofa and an elegant armchair. A dark coffee table sits at the center, while a dining table is visible in the background. Natural light illuminates the room through the windows, enhancing the cozy atmosphere.

Apartment in Woburn

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

4.96 out of 5 average rating, 73 reviews

An individual is skating on a frozen pond in front of a dark blue cottage adorned with solar panels. The cottage is surrounded by trees and snow-covered ground, creating a serene winter scene.

Cottage in Winchester

The Little House - a historic New England cottage.

This old fashioned New England cottage in a pocket of wooded suburbs just 9 miles from Logan Airport. 4 miles from Lexington Green where the revolutionary war began. Inside the 128 beltway, its an oasis of calm in the heart of Metro Boston. Keyless entry for easy check in. A highly sought location for ice skating in winter. In summer, enjoy a chorus of frogs every night & ample wildlife sightings. Your hosts live next door, in a quiet, family neighborhood. Kids are welcome, parties are not.

5 out of 5 average rating, 156 reviews

A comfortable living room is showcased with a blue sofa and two light-colored armchairs. A coffee table sits in the center, adorned with decorative items. Warm wood flooring complements the subtle hues of the walls, while soft lighting enhances the welcoming atmosphere.

Apartment in Woburn

Charming 1 BR private entrance apt commuters dream

Newly renovated, spacious 1 B/R apartment. Featuring a private entrance, kitchen with all new stainless-steel appliances, eating/office area, living room and separate bedroom with a Queen-sized bed, streaming cable & WIFI connections, exclusive outdoor space and off-street-parking. Minutes to Rt 95, Rt 128, Rt 93. Easy drive to all major local business, hospitals, mass transportation , airport & commuter rail less than 2 miles. Minutes to Woburn center, Winchester center, shopping & dining.

4.98 out of 5 average rating, 165 reviews

A spacious living area features a comfortable sofa adorned with textured pillows and a cozy throw. A wooden coffee table holds magazines and a remote. Natural light enters through a nearby window, enhancing the soft, neutral decor.

Guest suite in Woburn

Relaxing and Comfortable Home Away From Home

Privacy and comfort in complete lower level of this home. Private entrance and no shared space all within 5 minutes of shopping/restaurants and major highways. The space features a large kitchen w/dining area for 4pp, 1 bedroom with queen sized bed , living room with 65 inch tv with full cable. 1 full Bathroom with shower and tub. Washer and dryer are also included. Professionally maintained and enclosed backyard and patio area for outdoor seating.Full sized bed in the bonus room.

4.93 out of 5 average rating, 163 reviews

A private outdoor area features a spacious hot tub surrounded by wooden walls and deck flooring. Soft lighting is provided by string lights overhead. A small table sits nearby for convenience, and a patterned rug adds a touch of comfort to the space.

Apartment in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

Welcome to your romantic 1-bedroom apartment in Woburn, the ultimate escape for couples looking for relaxation and charm. Enjoy a private jacuzzi 🛁 and a cozy fire pit 🔥—ideal for creating unforgettable memories. Step right out from the bedroom to the jacuzzi and outdoor space, allowing you to unwind in the soothing waters while enjoying the warm ambiance of the fire pit. Perfect for a romantic retreat, this intimate space provides everything you need for a truly enchanting stay.

4.92 out of 5 average rating, 555 reviews

The spacious bedroom features a king-sized bed with a dark quilt and layered patterned bedding. Soft lamps provide ambient lighting on either side of the bed, which is set against a wall adorned with dark curtains. A flat-screen TV is positioned across from the bed, with an air conditioning unit nearby.

Guest suite in Melrose

Private Suite-Free Parking,near Boston Airp-Train

--> 7 miles N of Boston & a near the subway, beaches, airport & Salem (93, 95 & Rte 1), you’ll find the charming city of Melrose. The Melrosian Suite is nestled behind other houses & surrounded by gardens and trees. Wake up to the sounds of chirping birds instead of Boston’s noise and congestion. 225 acres of ponds, trails & conservation lands are at top of street w/ distant views of Boston & the ocean. Before booking, check out info required when you book & house rules.

4.89 out of 5 average rating, 216 reviews

The exterior of a historic gothic cottage is shown, featuring a stone facade and multiple large windows. Surrounding greenery and trees provide shade to the yard, enhancing the serene setting. A well-maintained lawn with a variety of plants is visible in the foreground.

Guest suite in Medford

Beautiful 1 Bedroom, 1 Bathroom in Medford

Come stay in this recently renovated, very comfortable space situated in a quiet neighborhood across the street from the Brooks Estate woods, just outside of Boston. The house itself is a historical gothic cottage built in 1856 and is the 2nd oldest home in the area. The space is in a historic single family home and both the bedroom and bathroom are 100% PRIVATE and separated from the rest of the house with a private entrance. It's on the first floor so there are no stairs!

4.97 out of 5 average rating, 134 reviews

A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.

Guest suite in Lexington

Modern Farmhouse Suite in Historic Lexington

Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

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Popular amenities for Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Winchester

Private room in Arlington

4.77 out of 5 average rating, 56 reviews

Jo's Beach Queen shared apt- parking

4.83 out of 5 average rating, 24 reviews

A private room features a spacious bed dressed with a soft blanket. A television is positioned on the opposite wall. Natural light streams in from a nearby window, while a light-colored wood cabinet is included for storage.

Private room in Woburn

A quiet place to spend a few days

Private room in Billerica

4.81 out of 5 average rating, 138 reviews

RM #1; Wi-Fi, A/C & 1 parking

Private room in Winchester

A three-story historical house with a yellow exterior features a wraparound porch and multiple gables. Lush greenery surrounds the property, and a driveway accommodates a parked vehicle. The evening sky casts a soft glow over the charming architecture.

5 out of 5 average rating, 7 reviews

Bedroom in historical house

Private room in Lexington

4.95 out of 5 average rating, 19 reviews

Private Bedroom with One full bed

4.98 out of 5 average rating, 44 reviews

A cozy bedroom with green walls features a bed draped in a patterned green blanket. A lamp provides illumination beside the bed, and a small desk is positioned near a window adorned with dark blinds. A radiator is visible against one wall.

Private room in Medford

"Tree-house" single room in cozy home, Medford

4.82 out of 5 average rating, 198 reviews

A cozy bedroom features a spacious bed with white linens, set against gray walls. Two windows are dressed with dark curtains, allowing natural light to filter in. A round mirror is mounted on the wall, complementing the minimalist decor.

Private room in Medford

Lovely Queen Bed in Tufts / Green Line Train Stop